Patrick Roy Won Three Conn Smythe Trophies, More Than Any Player

Patrick Roy won the Conn Smythe Trophy as playoff MVP three times, in 1986, 1993 and 2001, which no other player has done. He won four Stanley Cups with two franchises, and holds the records for playoff games and playoff wins.

He finished with 151 playoff wins in 247 playoff games, both records. The first Conn Smythe came at 20, as a rookie, when he won all fifteen Montreal victories of the 1986 postseason. He is the youngest player ever to win the award, and only the second rookie to be named playoff MVP.

The 1993 run is the one that defines him. Montreal won ten consecutive overtime games in those playoffs, an entire postseason of sudden death decided by one goaltender refusing to concede the next one. Ten straight, in a format where a single mistake ends the night. He saved 92.9 percent of what he faced that spring, and after Montreal lost the first two games of the opening round it won eleven in a row. He won the Conn Smythe again, and Montreal has not won a Cup since.

He then went to Colorado and did it a third time, in 2001, fifteen years after the first. That is the strongest thing on his resume: not that he was hot for one spring, which happens to goaltenders, but that he was the best player in a championship run three separate times across three decades and two organizations.

He also changed the mechanics. Roy popularized the butterfly, dropping to both knees and sealing the ice with his pads rather than staying upright, and a generation of goaltenders was coached into it. The position looks the way it does because of him, with the eventual side effect that hip injuries became the occupational hazard of the job.

Martin Brodeur has more wins, more shutouts and essentially every regular season record the position offers, and he played behind the best defensive system of his era. Dominik Hasek had the highest peak of anyone: back-to-back Hart Trophies in 1997 and 1998, the only goaltender to win the MVP award twice, on teams that had no business contending.

Brodeur owns the record book and Hasek owns the peak. Roy owns the games that decide championships, which for a goaltender is the job.

The verdict: Roy for winning. Brodeur for the records. Hasek for the peak.